| TT Cup Ukraine | 2021/12/01 15:10 | Sergey Demidov v Andriy Chupovskiy | L | 2-3 |
| TT Cup Ukraine | 2021/10/22 01:05 | Andriy Chupovskiy v Sergey Demidov | L | 3-0 |
| TT Cup Ukraine | 2021/10/21 22:05 | Andriy Chupovskiy v Sergey Demidov | L | 3-1 |
| TT Cup Ukraine | 2021/06/20 07:15 | Sergey Demidov v Andriy Chupovskiy | L | 0-3 |
| TT Cup Ukraine | 2021/06/19 08:25 | Sergey Demidov v Andriy Chupovskiy | L | 1-3 |
| TT Cup Ukraine | 2021/05/01 21:00 | Andriy Chupovskiy v Sergey Demidov | L | 3-0 |
| TT Cup Ukraine | 2021/05/01 03:20 | Sergey Demidov v Andriy Chupovskiy | L | 0-3 |
| TT Cup Ukraine | 2021/05/01 00:20 | Sergey Demidov v Andriy Chupovskiy | L | 1-3 |
| TT Cup Ukraine | 2022/01/06 17:00 | Alexander Lysak v Sergey Demidov | L | 3-0 |
| TT Cup Ukraine | 2022/01/06 15:50 | Kukava Nodar v Sergey Demidov | L | 3-1 |
| TT Cup Ukraine | 2022/01/06 15:10 | Viacheslav Yarovoi v Sergey Demidov | L | 3-0 |
| TT Cup Ukraine | 2022/01/06 14:35 | Andrey Movin v Sergey Demidov | L | 3-2 |
| TT Cup Ukraine | 2022/01/05 17:30 | Alexander Lysak v Sergey Demidov | W | 1-3 |
| TT Cup Ukraine | 2022/01/05 17:00 | Sergey Demidov v Alexander Lysak | L | 2-3 |
| TT Cup Ukraine | 2022/01/05 16:25 | Kukava Nodar v Sergey Demidov | L | 3-2 |
| TT Cup Ukraine | 2022/01/05 15:45 | Yuriy Tarasov v Sergey Demidov | L | 3-1 |
| TT Cup Ukraine | 2022/01/14 02:05 | Anton Maslov v Andriy Chupovskiy | L | 3-2 |
| TT Cup Ukraine | 2022/01/14 01:05 | Mykhailo Beley v Andriy Chupovskiy | L | 3-2 |
| TT Cup Ukraine | 2022/01/14 00:35 | Andriy Chupovskiy v Kukava Nodar | L | 0-3 |
| TT Cup Ukraine | 2022/01/13 23:05 | Anton Maslov v Andriy Chupovskiy | W | 1-3 |
| TT Cup Ukraine | 2022/01/13 22:05 | Mykhailo Beley v Andriy Chupovskiy | W | 1-3 |
| TT Cup Ukraine | 2022/01/13 21:35 | Andriy Chupovskiy v Kukava Nodar | L | 1-3 |
| TT Cup (2022) | 2022/01/09 14:40 | Oleksandr Soloviov v Andriy Chupovskiy | L | 3-2 |
| TT Cup Ukraine | 2022/01/09 14:05 | Anton Maslov v Andriy Chupovskiy | L | 3-0 |